diff --git a/docs/release-control/v6/internal/subsystems/ai-runtime.md b/docs/release-control/v6/internal/subsystems/ai-runtime.md
index 6f4ac3008..a62696006 100644
--- a/docs/release-control/v6/internal/subsystems/ai-runtime.md
+++ b/docs/release-control/v6/internal/subsystems/ai-runtime.md
@@ -99,6 +99,11 @@ runtime cost control, and shared AI transport surfaces.
    replay one-shot finding handoff, approval, autonomous-mode, or other scoped
    send options. Scoped context replay remains owned by explicit session
    handoff metadata or queued follow-up edit state.
+   Failed-turn retry is part of that same local chat-runtime boundary: a
+   retryable in-memory assistant error may replay the original user turn's
+   structured mentions, finding id, approval override, handoff resources,
+   handoff actions, and handoff metadata, but must not reconstruct scoped
+   context from prompt history or saved transcript prose.
    Assistant output hygiene is part of the same boundary: provider reasoning
    and raw serialized tool-call artifacts must never render as assistant
    transcript prose. Reasoning/thinking deltas may update neutral progress
diff --git a/frontend-modern/src/components/AI/Chat/__tests__/useChat.test.ts b/frontend-modern/src/components/AI/Chat/__tests__/useChat.test.ts
index ccd99acca..29dc64123 100644
--- a/frontend-modern/src/components/AI/Chat/__tests__/useChat.test.ts
+++ b/frontend-modern/src/components/AI/Chat/__tests__/useChat.test.ts
@@ -265,6 +265,72 @@ describe('useChat', () => {
       dispose();
     });
 
+    it('retryMessage preserves mentions, finding handoff, and scoped send options', async () => {
+      mockChat.mockRejectedValueOnce(new Error('server error')).mockResolvedValueOnce(undefined);
+      const { value: chat, dispose } = withRoot(() => useChat({ sessionId: 'sess' }));
+
+      await chat.sendMessage(
+        'check this resource',
+        [{ id: 'vm-100', name: 'web-1', type: 'vm', node: 'pve-1' }],
+        'finding-42',
+        {
+          autonomousMode: false,
+          handoffContext: '[Patrol Finding Context]\nFinding ID: finding-42',
+          handoffResources: [
+            {
+              id: 'vm-100',
+              name: 'web-1',
+              type: 'vm',
+              node: 'pve-1',
+            },
+          ],
+          handoffActions: [
+            {
+              findingId: 'finding-42',
+              approvalId: 'approval-1',
+              approvalStatus: 'pending',
+            },
+          ],
+          handoffMetadata: {
+            kind: 'patrol_finding',
+          },
+        },
+      );
+
+      const failed = chat.messages().find((m) => m.role === 'assistant');
+      expect(failed?.error).toContain('server error');
+
+      chat.retryMessage(failed!.id);
+      await new Promise((r) => setTimeout(r, 0));
+
+      expect(mockChat).toHaveBeenCalledTimes(2);
+      const retryCall = mockChat.mock.calls[1];
+      expect(retryCall[0]).toBe('check this resource');
+      expect(retryCall[5]).toEqual([{ id: 'vm-100', name: 'web-1', type: 'vm', node: 'pve-1' }]);
+      expect(retryCall[6]).toBe('finding-42');
+      expect(retryCall[7]).toBe(false);
+      expect(retryCall[8]).toBe('[Patrol Finding Context]\nFinding ID: finding-42');
+      expect(retryCall[9]).toEqual([
+        {
+          id: 'vm-100',
+          name: 'web-1',
+          type: 'vm',
+          node: 'pve-1',
+        },
+      ]);
+      expect(retryCall[10]).toEqual([
+        {
+          findingId: 'finding-42',
+          approvalId: 'approval-1',
+          approvalStatus: 'pending',
+        },
+      ]);
+      expect(retryCall[11]).toEqual({
+        kind: 'patrol_finding',
+      });
+      dispose();
+    });
+
     it('handles AbortError silently (returns false, no notification)', async () => {
       const abortError = new Error('Aborted');
       abortError.name = 'AbortError';
diff --git a/frontend-modern/src/components/AI/Chat/hooks/useChat.ts b/frontend-modern/src/components/AI/Chat/hooks/useChat.ts
index 6689c357a..3f8c437b6 100644
--- a/frontend-modern/src/components/AI/Chat/hooks/useChat.ts
+++ b/frontend-modern/src/components/AI/Chat/hooks/useChat.ts
@@ -19,6 +19,7 @@ import type {
   PendingQuestion,
   PendingTool,
   WorkflowStatus,
+  ChatMessageRequestContext,
 } from '../types';
 
 const generateId = () => Math.random().toString(36).substring(2, 9);
@@ -257,6 +258,80 @@ export function useChat(options: UseChatOptions = {}) {
     return typeof id === 'string' ? id.trim() : '';
   };
 
+  const cloneMentions = (mentions?: ChatMention[]): ChatMention[] | undefined =>
+    mentions?.map((mention) => ({ ...mention }));
+
+  const cloneSendOptions = (
+    sendOptions?: SendMessageOptions,
+  ): ChatMessageRequestContext | undefined => {
+    if (!sendOptions) return undefined;
+
+    const requestContext: ChatMessageRequestContext = {};
+    if (typeof sendOptions.autonomousMode === 'boolean') {
+      requestContext.autonomousMode = sendOptions.autonomousMode;
+    }
+    if (sendOptions.handoffContext) {
+      requestContext.handoffContext = sendOptions.handoffContext;
+    }
+    if (sendOptions.handoffResources?.length) {
+      requestContext.handoffResources = sendOptions.handoffResources.map((resource) => ({
+        ...resource,
+      }));
+    }
+    if (sendOptions.handoffActions?.length) {
+      requestContext.handoffActions = sendOptions.handoffActions.map((action) => ({ ...action }));
+    }
+    if (sendOptions.handoffMetadata) {
+      requestContext.handoffMetadata = { ...sendOptions.handoffMetadata };
+    }
+
+    return Object.keys(requestContext).length > 0 ? requestContext : undefined;
+  };
+
+  const buildRequestContext = (
+    mentions?: ChatMention[],
+    findingId?: string,
+    sendOptions?: SendMessageOptions,
+  ): ChatMessageRequestContext | undefined => {
+    const requestContext: ChatMessageRequestContext = {
+      ...(cloneSendOptions(sendOptions) || {}),
+    };
+    const clonedMentions = cloneMentions(mentions);
+    if (clonedMentions?.length) {
+      requestContext.mentions = clonedMentions;
+    }
+    if (findingId) {
+      requestContext.findingId = findingId;
+    }
+
+    return Object.keys(requestContext).length > 0 ? requestContext : undefined;
+  };
+
+  const sendOptionsFromRequestContext = (
+    request?: ChatMessageRequestContext,
+  ): SendMessageOptions | undefined => {
+    if (!request) return undefined;
+
+    const sendOptions: SendMessageOptions = {};
+    if (typeof request.autonomousMode === 'boolean') {
+      sendOptions.autonomousMode = request.autonomousMode;
+    }
+    if (request.handoffContext) {
+      sendOptions.handoffContext = request.handoffContext;
+    }
+    if (request.handoffResources?.length) {
+      sendOptions.handoffResources = request.handoffResources.map((resource) => ({ ...resource }));
+    }
+    if (request.handoffActions?.length) {
+      sendOptions.handoffActions = request.handoffActions.map((action) => ({ ...action }));
+    }
+    if (request.handoffMetadata) {
+      sendOptions.handoffMetadata = { ...request.handoffMetadata };
+    }
+
+    return Object.keys(sendOptions).length > 0 ? sendOptions : undefined;
+  };
+
   const applyStreamSessionId = (streamSessionId: string) => {
     if (!streamSessionId) return;
     const previousSessionId = sessionId();
@@ -633,6 +708,7 @@ export function useChat(options: UseChatOptions = {}) {
       content: trimmedPrompt,
       timestamp,
       delivery: 'queued',
+      request: buildRequestContext(mentions, findingId, sendOptions),
     };
 
     const queuedFollowUp: QueuedFollowUp = {
@@ -674,6 +750,7 @@ export function useChat(options: UseChatOptions = {}) {
       role: 'user',
       content: trimmedPrompt,
       timestamp: new Date(),
+      request: buildRequestContext(mentions, findingId, sendOptions),
     };
 
     const assistantId = generateId();
@@ -1026,9 +1103,15 @@ export function useChat(options: UseChatOptions = {}) {
     if (userIdx < 0) return;
     const prompt = msgs[userIdx].content;
     if (!prompt.trim()) return;
+    const request = msgs[userIdx].request;
     const removeIds = new Set([msgs[userIdx].id, assistantMessageId]);
     setMessages((prev) => prev.filter((m) => !removeIds.has(m.id)));
-    void sendMessage(prompt);
+    void sendMessage(
+      prompt,
+      cloneMentions(request?.mentions),
+      request?.findingId,
+      sendOptionsFromRequestContext(request),
+    );
   };
 
   return {
diff --git a/frontend-modern/src/components/AI/Chat/types.ts b/frontend-modern/src/components/AI/Chat/types.ts
index 185c10559..6e5315662 100644
--- a/frontend-modern/src/components/AI/Chat/types.ts
+++ b/frontend-modern/src/components/AI/Chat/types.ts
@@ -1,4 +1,10 @@
 // Chat component types
+import type {
+  ChatHandoffAction,
+  ChatHandoffMetadata,
+  ChatHandoffResource,
+  ChatMention,
+} from '@/api/aiChat';
 
 export interface ToolExecution {
   name: string;
@@ -109,11 +115,22 @@ export interface WorkflowStatus {
   tool?: string;
 }
 
+export interface ChatMessageRequestContext {
+  mentions?: ChatMention[];
+  findingId?: string;
+  autonomousMode?: boolean;
+  handoffContext?: string;
+  handoffResources?: ChatHandoffResource[];
+  handoffActions?: ChatHandoffAction[];
+  handoffMetadata?: ChatHandoffMetadata;
+}
+
 export interface ChatMessage {
   id: string;
   role: 'user' | 'assistant';
   content: string;
   delivery?: 'sent' | 'queued';
+  request?: ChatMessageRequestContext;
   interruption?: 'stopped' | 'replaced';
   // Clean, user-facing error for a failed turn. Rendered as a distinct error
   // block (not as answer content) so partial streamed content is preserved and